Compare Sheffield Cottage Rentals

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Featured Sheffield Cottages

The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

$362 nightly
The price is $404 total per night
$404 total
Oct 5 - Oct 6
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Free WiFi
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2 out of 5
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Kitchen
Pet friendly
Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Two Bedroom Cottage Close To Town

Two Bedroom Cottage Close To Town

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
The Cottage at Highland Lake, year-round, waterfront with a boat dock

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Free WiFi
Idillic summer getaway in Litchfield Hills, CT.

Idillic summer getaway in Litchfield Hills, CT.

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Light-filled cottage

Light-filled cottage

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Creekside Cottage The Fitz House Red Hook NY

Creekside Cottage The Fitz House Red Hook NY

Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Stylish Pine Plains Home Near Parks & Hiking!

Stylish Pine Plains Home Near Parks & Hiking!

3 out of 5
Guests of this cottage enjoy features like free WiFi in public areas. Free parking is available if you drive.
Kitchen
Washer
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Sheffield

    Wilder House Berkshires

    Wilder House Berkshires

    48 S Main Street, Sheffield, MA
    $173 nightly
    The price is $193 total per night from Oct 30 to Oct 31
    $193 total
    Oct 30 - Oct 31
    Total with taxes and fees
    9.6/10 Exceptional! (35 reviews)
    Guesthouse Cabin vacation rentals in Berkshire County

    Guesthouse Cabin vacation rentals in Berkshire County

    Sheffield
    $622 nightly
    The price is $695 total per night from Oct 5 to Oct 6
    $695 total
    Oct 5 - Oct 6
    Total with taxes and fees
    10/10 Exceptional! (9 reviews)
    Antique Farmhouse Totally Restored

    Antique Farmhouse Totally Restored

    Sheffield
    9.8/10 Exceptional! (58 reviews)

Cottages

Book a cottage in Sheffield
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Sheffield. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Sheffield better.

Cottage apartments in Sheffield range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Sheffield
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Sheffield and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Sheffield cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Sheffield. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Sheffield Cottages essential information

Accommodation
121 Cottages
Lowest Price
$193
Highest Price
$695
Popular accommodation
The Blue Elm - A Historic Berkshire Cottage, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Summer Lake Cottage, private beach, Berkshire Hills, small village, Two Bedroom Cottage Close To Town, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Idillic summer getaway in Litchfield Hills, CT., Light-filled cottage, Creekside Cottage The Fitz House Red Hook NY, Stylish Pine Plains Home Near Parks & Hiking!